I like how guys share their experiences on this site. These are things we could never talk about until we had gay friends because we weren't in the 100% straight world. Even now, I haven't shared some of these stories so it's good to get them out there. It's amazing how many of us have had similar experiences but in different places.
I shared this with another guy on here this week. For me college was a time of discovery. I had an affair with a 34 year old married guy. I guess it was more of an affair for him than me since I wasn't in a relationship at the time. He was 6'4", good looking. Italian, dark hair, olive skin, classic looks, and athletic build. My friends tell me the way we met sounds like a cheesy gay porn movie.
I was picking up some briefs, aka tightie whities, in a department store. As I was going through the stack looking for several in my size he came up and started looking at underwear. I thought, "Fuck! He's hot. And he's buying underwear!" Plus he was wearing a suit (I've always had a thing for good looking guys in suits!) When I had mine picked out I turned around to go to the register and he said, "What do you think, gray or black?" as he held up a package in each hand. I was like did he just ask me that?!! I had never been hit on in public so was nervous... plus I didn't have much experience with guys and times were different. I didn't really know how to respond but wanted to since he was so hot and I was trying to get comfortable with myself being gay. I responded, "Gray if you're working out and black for all other times." He smiled and said, "I guess I'll have to get both." He was so handsome and his smile melted me. We then both walked up to the cash register. There were two sales associates who rang us up at the same time.
We walked out of the underwear department at the same time and towards the same door to the parking lot. Since he wasn't saying anything I thought maybe he wasn't hitting on me and was asking a serious question. But I also knew I had always kicked myself for not going for it, being more forward, so I decided to test the waters. I asked him, "So, what color are you wearing now?" He laughed and smiled and said, "White. Do you want to see? I replied, "Yes." He smiled and said, "And I guess you're wearing white?" And I responded, "Do you want to see?" He just smiled. I wasn't sure if he was just playing or not.
When we got out to the parking lot he said, "I'm over here." My heart started racing. I scored but this was also the first time I'd done anything like this. We went to his BMW and got in. He look around and checked that no one was around. He unbuckled his belt, unbuttoned the waistband, unzipped and spread open the fly of his trousers. He was wearing white Calvin Klein briefs. He reached into his trousers and pulled out a softball sized bulge. He then said, "Your turn" and I did the same although I didn't quite have a softball size bulge!
I said, "Black briefs will definitely look good on you" as I looked at his hairy lower stomach and wondered what he was packing. He said he agreed. I then thought to myself, you just need to go for it, so I asked, "Do I get to see what's in your briefs?" He smiled, pulled down the waistband with his left thumb exposing a thick dark bush and the base of his thick cock. He reached into his briefs with his right hand and pulled out his big dick and his balls. His cock was somewhere between soft and semi, a good six inches at this point and thick. It was quickly stretching out! He then told me it was my turn. I pulled out my dick which was getting hard and my balls. He asked if he could feel my cock and I told him yes. I let him feel my dick and balls for a couple of minutes. By now he was boned up and his hard dick was beautiful-- long, super thick, perfectly shaped with a slight banana curve. I reached over and felt him off.
After a few minutes of each of us feeling each other I told him I was getting a little nervous sitting in his car doing this. I asked him if we could go to his place. That's when he told me he was married and had kids. He then asked if I'd be interested in going to the hotel across the street. I said yes and we went to the hotel and he got a room. We quickly got naked. He told me what a nice body I had and here I was standing in front of him thinking he's the hottest guy I've ever been with! We made out and sucked each other's dick and then jacked off to completion. He shot a huge load, about twice as much as mine. Four to five big squirts onto his hairy chest and stomach.
As we cleaned up in the bathroom we started talking about other stuff and he seemed like a really good guy. We continued to talk as he drove me back to my car. He gave me his work number and said to call him if I was interested in getting together again. I called him the next day.
We got together for about four months. We only met in hotels. Sometimes for an hour or two, sometimes most of the day and twice an over nighter when his family was away. We talked a lot, watched movies or TV shows and had lots of sex, including a lot of fucking each other. It ended when his company transferred him. During our last get together he told me how much he liked me. His eyes got red and tears welled up and I knew he wanted to say more but couldn't because of his situation and the times.
I always wondered what happened to him. Really nice guy, handsome, hot fit body, big dick... still in the top 3 I've had in my ass! And the sex was great!!